1-methyl-5-aminoacridine and process for preparing it



. the subject-matter of Patented Nov. 22, 1949 UNITED STATES PATENT OFFICE l-METHYL-S-AIHINOACRIDINE AND PROC- ESS FOR PREPARING IT John Edwin Rogers Fal New South Wales, A

of Delaware N Drawing. Applicatio A rial No. 647,992. In

ling Drug Inc., Wilm k, Waverton,

near Sydney,

ustralia, assignor to Sterington, Del., a

corporation 11 February 15, 1946, Seustralia March- 3, 1945 3 Claims. (Cl. 260279) This invention has relevance to improvements to the process for the preparation of 5-amino acridines from diphenylamine-2-carboxylic acids.

In the said 5-amino acridines which have the following general formula:

NH: 6 I5 4 this application.

However, by the literature published on the subject it is not disclosed that the preparation of the said 5-amino acridines has been accomplished in the one vessel without the isolation of either the 5-chloro or 5-phenoxy acridines, and that an inert solvent can be used in the preparation of 5- hloro acridine.

"*In this invention, the 5-amino acridines are prepared in the one vessel without the isolation of the 5-chloroor 5-phenoxy acridines.

This is efiected by reaction of phosphorus pentachloride or phosphorus oxychloride with diphenylamine-2-carboxyllc acids or substituted diphenylamine-Z-carboxylic acids in a solvent which will not By way of illustration the following examples are given for the preparation of amino acridines according to the invention.

5 -AMINOACRIDINE Example 1 50 grams of diphenylamine-2-carboxylic acid are stirred with 125 cc. of monochlorobenzene, and 50 grams of phosphorus pentachloride (or grams of The flask is connected to a suitable gas trap. When gas evolution ceases, about of the is distilled off at atmospheric withdrawn should give a definite blue color to wet, red litmus. The bath is now at 76 C. 36 grams of powdered ammonium carbonate are now added as quickly as possible. The internal temperature is then raised quickly to 120 C. and maintained there for two hours with continual stirring.

The reaction vessel is then removed from the oil bath, the contents cooled to about 0.,

with acetone, the melting point is 232.5 C. (239.5 C. corrected) and the yield is 38 grams (83.5%).

1-METHYL-5-AMINO-ACRIDINE Example 2 To 8 grams of Z-methyl-diphenylamine-Z carboxylic acid in 20 cc. monochlorobenzene, 7.5

grams phosphorus pentachloride are added, and

the method described in Example 1 abovementioned is followed. 9 grams of sodium carbonate are used for the neutralization mentioned. 5.4 grams ammonium carbonate are used for the amination. The ire-precipitation is carried out at pH. 8.4. and the l-methyl-S-amino-acridine precipitated is filtered off, and dried in the manner beforementioned. It may be crystallised either from benzene or 59% alcohol. Yield. 4 gms, M. P. 192 C.

What I claim as my invention and desire to' 3. 1-methyl-5-amino acridine JOHN EDWIN ROGERS FALK.

REFERENCES. CITED.-

Thefollowing references are of record in the file of this patent:

UNITED STATES PATENTS Name Date Fehrle Nov. 1, 1932 OTHER REFERENCES Magidson et al., Berichte, vol. 66, pages 866- 8'72 (1933).

Glen et al., J. Prakt, Chem., vol. 153, pages 200-224 (1939).,

Gerchuk et al., J. pages 948-953 (1941) 3'7, page 3'78; 1943).

Albert et al., J. Soc. Chem. Ind. (Transactions), vol. 60, pages 120-123 (May 1941).

Smith, Organic Syntheses, vol. 22, pages 5-8 (John Wiley, New York 1942).

Number- Gen. Chem. (USSR), vol. 11, (cited in Chem. Obs, vol. 

